#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150337.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150337
loop_
_publ_author_name
'Arany, Andrea'
'Crowley, Patrick J.'
'Fawcett, John'
'Hursthouse, Michael B.'
'Kariuki, Benson M.'
'Light, Mark E.'
'Moralee, Andrew C.'
'Percy, Jonathan M.'
'Salafia, Vittoria'
_publ_section_title
;
 Highly-functionalised difluorinated (hydroxymethyl)conduritol
 analogues via the Diels-Alder reactions of a difluorinated dienophile.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              455
_journal_page_last               465
_journal_paper_doi               10.1039/b314314g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C16 H23 F2 N O5'
_chemical_formula_sum            'C16 H23 F2 N O5'
_chemical_formula_weight         347.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.881(3)
_cell_angle_beta                 102.152(3)
_cell_angle_gamma                108.900(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8012(5)
_cell_length_b                   8.9989(5)
_cell_length_c                   14.1190(9)
_cell_measurement_reflns_used    1709
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      55.17
_cell_measurement_theta_min      3.27
_cell_volume                     897.60(10)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4530
_diffrn_reflns_theta_full        55.17
_diffrn_reflns_theta_max         55.17
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.9134
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS in SAINTPLUS'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0052(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0992P)²+0.3578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1693
_reflns_number_gt                1709
_reflns_number_total             2041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314314g.txt
_cod_data_source_block           14b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150337
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2485(4) 0.8299(3) 0.7076(2) 0.0548(8) Uani 1 1 d . . .
C2 C 0.0435(5) 0.7912(4) 0.6432(3) 0.0662(10) Uani 1 1 d . . .
C3 C 0.0724(5) 0.8409(4) 0.5475(3) 0.0719(10) Uani 1 1 d . . .
H3 H -0.0355 0.8548 0.5048 0.086 Uiso 1 1 calc R . .
C4 C 0.1524(5) 0.7339(4) 0.4990(3) 0.0756(10) Uani 1 1 d . . .
H4 H 0.0905 0.6536 0.4425 0.091 Uiso 1 1 calc R . .
C5 C 0.3288(5) 0.7741(4) 0.5513(2) 0.0670(10) Uani 1 1 d . . .
C6 C 0.3595(5) 0.9102(4) 0.6349(2) 0.0621(9) Uani 1 1 d . . .
C7 C 0.4216(5) 0.6825(4) 0.7841(2) 0.0617(9) Uani 1 1 d . . .
C8 C 0.2672(5) 0.3898(4) 0.7302(3) 0.0834(12) Uani 1 1 d . . .
H8A H 0.3173 0.3053 0.7199 0.100 Uiso 1 1 calc R . .
H8B H 0.2188 0.4101 0.6659 0.100 Uiso 1 1 calc R . .
C9 C 0.1109(7) 0.3334(6) 0.7762(5) 0.1236(18) Uani 1 1 d . . .
H9A H 0.1590 0.3208 0.8420 0.185 Uiso 1 1 calc R . .
H9B H 0.0218 0.2323 0.7375 0.185 Uiso 1 1 calc R . .
H9C H 0.0503 0.4106 0.7792 0.185 Uiso 1 1 calc R . .
C10 C 0.5757(6) 0.5177(5) 0.8596(4) 0.0992(14) Uani 1 1 d . . .
H10A H 0.6262 0.6072 0.9156 0.119 Uiso 1 1 calc R . .
H10B H 0.5308 0.4196 0.8838 0.119 Uiso 1 1 calc R . .
C11 C 0.7182(8) 0.5133(7) 0.8134(5) 0.1361(19) Uani 1 1 d . . .
H11A H 0.6667 0.4271 0.7564 0.204 Uiso 1 1 calc R . .
H11B H 0.8169 0.4965 0.8591 0.204 Uiso 1 1 calc R . .
H11C H 0.7679 0.6131 0.7932 0.204 Uiso 1 1 calc R . .
C12 C 0.2771(5) 0.9352(4) 0.8058(3) 0.0647(9) Uani 1 1 d . . .
C13 C 0.2179(7) 0.9353(6) 0.9640(3) 0.1040(14) Uani 1 1 d . . .
H13A H 0.3452 1.0097 0.9947 0.125 Uiso 1 1 calc R . .
H13B H 0.1356 0.9964 0.9556 0.125 Uiso 1 1 calc R . .
C14 C 0.1621(9) 0.8241(7) 1.0258(4) 0.142(2) Uani 1 1 d . . .
H14A H 0.0333 0.7553 0.9972 0.214 Uiso 1 1 calc R . .
H14B H 0.1752 0.8817 1.0902 0.214 Uiso 1 1 calc R . .
H14C H 0.2402 0.7606 1.0313 0.214 Uiso 1 1 calc R . .
C15 C 0.4699(6) 0.7005(5) 0.5384(3) 0.0931(12) Uani 1 1 d . . .
H15A H 0.4139 0.6103 0.4839 0.140 Uiso 1 1 calc R . .
H15B H 0.5115 0.6653 0.5977 0.140 Uiso 1 1 calc R . .
H15C H 0.5753 0.7783 0.5254 0.140 Uiso 1 1 calc R . .
C16 C 0.5570(5) 1.0303(4) 0.6758(3) 0.0801(11) Uani 1 1 d . . .
H16A H 0.6044 1.0693 0.6225 0.120 Uiso 1 1 calc R . .
H16B H 0.6358 0.9797 0.7095 0.120 Uiso 1 1 calc R . .
H16C H 0.5567 1.1183 0.7213 0.120 Uiso 1 1 calc R . .
N1 N 0.4193(4) 0.5349(3) 0.7891(2) 0.0749(9) Uani 1 1 d . . .
O1 O 0.2356(3) 0.9870(3) 0.59069(18) 0.0755(7) Uani 1 1 d . . .
O2 O 0.2633(3) 0.6781(2) 0.71935(15) 0.0587(6) Uani 1 1 d . . .
O3 O 0.5456(3) 0.8073(3) 0.82990(17) 0.0768(8) Uani 1 1 d . . .
O4 O 0.3453(4) 1.0795(3) 0.82381(18) 0.0830(8) Uani 1 1 d . . .
O5 O 0.2084(3) 0.8486(3) 0.86819(17) 0.0756(7) Uani 1 1 d . . .
F1 F -0.0695(3) 0.6349(2) 0.62938(16) 0.0824(7) Uani 1 1 d . . .
F2 F -0.0430(3) 0.8763(3) 0.68722(17) 0.0906(7) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C12 111.9(2) . . ?
O2 C1 C2 106.0(2) . . ?
C12 C1 C2 108.7(3) . . ?
O2 C1 C6 113.2(2) . . ?
C12 C1 C6 116.8(3) . . ?
C2 C1 C6 98.7(2) . . ?
F2 C2 F1 105.2(3) . . ?
F2 C2 C3 111.2(3) . . ?
F1 C2 C3 112.6(3) . . ?
F2 C2 C1 111.0(3) . . ?
F1 C2 C1 113.6(2) . . ?
C3 C2 C1 103.4(3) . . ?
O1 C3 C4 102.7(3) . . ?
O1 C3 C2 97.4(3) . . ?
C4 C3 C2 108.4(3) . . ?
C5 C4 C3 107.1(3) . . ?
C4 C5 C15 129.6(3) . . ?
C4 C5 C6 105.4(3) . . ?
C15 C5 C6 125.0(3) . . ?
O1 C6 C16 110.4(3) . . ?
O1 C6 C5 102.5(3) . . ?
C16 C6 C5 116.8(3) . . ?
O1 C6 C1 99.6(2) . . ?
C16 C6 C1 119.6(3) . . ?
C5 C6 C1 105.4(3) . . ?
O3 C7 N1 126.3(3) . . ?
O3 C7 O2 122.6(3) . . ?
N1 C7 O2 111.1(3) . . ?
N1 C8 C9 113.5(4) . . ?
C11 C10 N1 110.2(4) . . ?
O4 C12 O5 124.1(3) . . ?
O4 C12 C1 124.5(3) . . ?
O5 C12 C1 111.3(3) . . ?
C14 C13 O5 109.5(4) . . ?
C7 N1 C8 123.5(3) . . ?
C7 N1 C10 118.2(3) . . ?
C8 N1 C10 118.3(3) . . ?
C6 O1 C3 96.5(2) . . ?
C7 O2 C1 116.5(2) . . ?
C12 O5 C13 117.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.433(3) . ?
C1 C12 1.513(5) . ?
C1 C2 1.567(5) . ?
C1 C6 1.573(5) . ?
C2 F2 1.351(4) . ?
C2 F1 1.361(4) . ?
C2 C3 1.512(5) . ?
C3 O1 1.456(4) . ?
C3 C4 1.482(5) . ?
C4 C5 1.324(5) . ?
C5 C15 1.487(5) . ?
C5 C6 1.515(5) . ?
C6 O1 1.443(4) . ?
C6 C16 1.507(5) . ?
C7 O3 1.214(4) . ?
C7 N1 1.333(4) . ?
C7 O2 1.359(4) . ?
C8 N1 1.458(4) . ?
C8 C9 1.476(6) . ?
C10 C11 1.411(7) . ?
C10 N1 1.467(5) . ?
C12 O4 1.205(4) . ?
C12 O5 1.327(4) . ?
C13 C14 1.428(7) . ?
C13 O5 1.453(5) . ?
